Just spitballing LL investments here...
Only about 10% of the LL.ca's are what I'd call actively being used as a website. The other 90% are pretty much up for sale. And many of those were probably grabbed early by the end users, so they didn't pay the 6-figure end user prices, or at the very least they paid very cheap price compared to today's average LL BIN of $150K CAD.
Lets say only 50% of the LL.ca's actively being used were bought in the aftermarket over the past 20 years at an end-user price. That is 1.7 LL.ca aftermarket sales per year on average, out of 676 total LL.ca domains. That's a 0.25% (0.0025) yearly sell rate. Project that out if you own just one LL, that would be 400 years on average before any specific one sells at an end-user type price.
Now lets say you were a genius and hand-registered all 676 of them, so that's just about $7500 / year in renewals. And if you sold 1.7 per year at say $100,000 CAD (very generous), that would be $170,000 on $7500 in expenses, or a bit more than a 20x multiple. 34 sales over 20 years is $3.4M - 20 years of renewals @ 7500/yr = $3.25M net or $162K/year net. That would have been a genius move indeed.
But what if you bought them in the aftermarket instead? Lets say you bought them all in the aftermarket at a cost of $5000 each. Do you think that would be a good investment?
That would be $3.38M for all 676 of them. Based on the previous assumptions, you still wouldn't have broken even, and that's without even considering the time value of money.
Bottom line, if you were buying LL's in the aftermarket at mid $XXXX prices, you would have to have bought a lot, been very selective, been a good salesman, had a little luck AND have been a very good and patient negotiator to have made money. Otherwise, owning a random LL or two is very much a lottery ticket, and more like a scratcher at that.